US4613669A - Preparation of 1,4-diketopyrrolo-[3,4-c]pyrroles - Google Patents

Preparation of 1,4-diketopyrrolo-[3,4-c]pyrroles Download PDF

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US4613669A
US4613669A US06/512,074 US51207483A US4613669A US 4613669 A US4613669 A US 4613669A US 51207483 A US51207483 A US 51207483A US 4613669 A US4613669 A US 4613669A
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formula
alkyl
compound
phenyl
mole
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Luigi Cassar
Abul Iqbal
Alain C. Rochat
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BASF Corp
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Ciba Geigy Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3415—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/004—Diketopyrrolopyrrole dyes

Definitions

  • the present invention relates to a process for the preparation of 1,4-diketopyrrolo[3,4-c]pyrroles which are valuable pigments.
  • a process for the preparation of 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole starting from benzonitrile and ethyl bromoacetate in the presence of activated zinc-copper couple is described in Tetrahedron Lett. 1974, 2549-52. However, the yields obtained up to now have been unsatisfactory.
  • the compounds of this invention as starting materials, the desired pyrrolo[3,4-c]-pyrrole pigments are obtained in substantially higher yield and purity.
  • the present invention provides a process for the preparation of 1,4-diketopyrrolo[3,4-c]pyrroles of the formula ##STR3## wherein each of R 1 and R 2 independently of the other is an isocyclic aromatic or non-basic heterocyclic aromatic radical, which process comprises reacting 1 mole of the compound of formula ##STR4## wherein M is a metal atom, Z is alkyl or aryl, X is halogen or acetate, and m is a value from 0 to 2, with 1 mole of a compound of the formula
  • R 1 and R 2 may be different or identical.
  • R 1 and R 2 as isocyclic aromatic radicals are preferably monocyclic to tetracyclic radicals, most preferably monocyclic or bicyclic radicals, i.e. phenyl, diphenylyl or naphthyl.
  • Non-basic heterocyclic aromatic radicals R 1 and R 2 are preferably monocyclic to tricyclic radicals. These radicals may be entirely heterocyclic or may contain a heterocyclic ring and one or more fused benzene rings, e.g. thienyl, furoyl, thiophenyl, coumarinyl or benzfuranyl.
  • Both the isocyclic and the heterocyclic aromatic radicals may contain the customary non-watersolubilising substituents such as:
  • Halogen atoms e.g. chlorine, bromine or fluorine atoms.
  • alkyl groups containing preferably 1 to 18, especially 1 to 12, more particularly 1 to 8 and, most preferably, 1 to 4, carbon atoms.
  • alkyl groups may contain non-watersolubilising substituents, e.g.
  • R 3 is alkyl, aryl such as naphthyl, or benzyl or benzyl substituted by halogen, alkyl or --O-alkyl, or is a heterocyclic radical;
  • R 4 and R 5 are hydrogen, alkyl or alkyl substituted by cyano or hydroxy, or is C 5 -C 6 cycloalkyl, aryl or heteroaryl, especially phenyl or phenyl substituted by halogen, alkyl or --O-alkyl, or wherein R 4 and R 5 together with the nitrogen atom form a 5- or 6-membered heterocyclic ring, e.g.
  • aryl radicals such as naphthyl or preferably phenyl or phenyl substituted by halogen, alkyl or --O-alkyl, or also non-basic heterocyclic aromatic radicals such as 2-thienyl or 6-benzimidazolonyl radicals.
  • this alkyl moiety may be branched or unbranched and contain preferably 1 to 18, especially 1 to 12, more particularly 1 to 8 and, most preferably, 1 to 4 carbon atoms.
  • unsubstituted or substituted alkyl groups are: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, tert-amyl, n-pentyl, n-hexyl, 1,1,3,3-tetramethylbutyl, n-heptyl, n-octyl, nonyl, decyl, undecyl, dodecyl, hydroxymethyl, trifluoromethyl, trifluoroethyl, cyanomethyl, methoxycarbonylmethyl, acetoxymethyl or benzyl.
  • R 6 is hydrogen, alkyl, or aryl such as naphthyl or preferably phenyl or phenyl substituted by halogen, alkyl or --O-alkyl, or is C 5 -C 6 cycloalkyl, aralkyl or a non-basic heterocyclic radical.
  • alkyl may contain a number of carbon atoms specified as preferred in (2) above.
  • R 6 are: methyl, ethyl, n-propyl, isopropyl, trifluoroethyl, phenyl, o-, m- or p-chlorophenyl, o-, m- or p-methylphenyl, ⁇ - or ⁇ -naphthyl, cyclohexyl, benzyl, thienyl or pyranylmethyl.
  • R 6 is as defined in (3) above.
  • Typical examples of R 6 are: methyl, ethyl, n-propyl, isopropyl, phenyl, o-, m- or p-chlorophenyl, o-, m- or p-methylphenyl, ⁇ - or ⁇ -naphthyl, cyclohexyl, benzyl, thienyl or pyranylmethyl.
  • R 3 is as defined in (2).
  • R 3 are: methyl, ethyl, isopropyl, tert-butyl, n-butyl, phenyl, benzyl or furfuryl.
  • R 6 is as defined in (3).
  • R 6 are: methyl, ethyl, tert-butyl, phenyl, o-, m- or p-chlorophenyl, o-, m- or p-methylphenyl or ⁇ - or ⁇ -naphthyl.
  • R 7 is hydrogen, alkyl, aryl, e.g. naphthyl or preferably phenyl or phenyl substituted by halogen, alkyl or --O-alkyl, or is C 5 -C 6 cycloalkyl, aralkyl or the radical --COR 3 , with two radicals --COR 3 together with the nitrogen atom being able to form a heterocyclic ring.
  • alkyl may contain a number of carbon atoms specified as preferred in (2) above.
  • Typical examples are: acetylamino, propionylamino, butyrylamino, benzoylamino, p-chlorobenzoylamino, p-methylbenzoylamino, N-methylacetylamino, N-methylbenzoylamino, N-succinimido or N-phthalimido.
  • R 3 is as defined in (2) above.
  • Typical examples of R 3 are: methyl, ethyl, phenyl, o-, m- or p-chlorophenyl, o-, m- or p-methylphenyl, ⁇ - or ⁇ -naphthyl.
  • R 4 and R 5 are as defined in (2).
  • R 4 and R 5 are: carbamoyl, N-methylcarbamoyl, N-ethylcarbamoyl, N-phenylcarbamoyl, N,N-dimethylcarbamoyl, N-methyl-N-phenylcarbamoyl, N- ⁇ -naphthylcarbamoyl or N-piperidylcarbamoyl.
  • R 8 is the radical of a coupling component or is a phenyl radical which is unsubstituted or substituted by halogen, alkyl or O-alkyl.
  • alkyl may contain a number of carbon atoms specified in (2) as preferred.
  • R 8 are: acetoacetarylide, pyrazolyl, pyridonyl, o- or p-hydroxyphenyl, o-hydroxynaphthyl, p-aminophenyl or p-N,N-dimethylaminophenyl radicals.
  • R 3 is as defined in (2) above.
  • R 3 are: methyl, ethyl, phenyl, o-, m- or p-chlorophenyl.
  • X and Y as halogen in the compounds of the formulae II and III may be chlorine, bromine or iodine.
  • Alkyl groups Z in the compounds of the formulae II and III can be branched or unbranched and contain preferably 1 to 12, in particular 1 to 8 and, most preferably, 1 to 5 carbon atoms.
  • alkyl groups are: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, tert-amyl, n-hexyl, n-heptyl, n-octyl and 1,1,3,3-tetramethylbutyl.
  • Z as aryl in the compounds of the formulae II and III is preferably unsubstituted phenyl or phenyl substituted by halogen such as chlorine, or C 1 -C 6 alkyl such as methyl, ethyl, isopropyl or tert-butyl, or C 1 -C 6 alkoxy such as methoxy or ethoxy.
  • Aryl is preferably unsubstituted phenyl.
  • M as metal atom in the compounds of the formula II can be in particular a monovalent, bivalent or trivalent metal atom, e.g. lithium, sodium, potassium, magnesium, calcium, zinc, copper or aluminium.
  • the preferred metal atom is zinc.
  • the preferred starting materials are compounds of the formula II, wherein R 1 is unsubstituted phenyl or naphthyl or phenyl or naphthyl which contain non-watersolubilising substituents.
  • More preferred starting materials are compounds of the formula II, wherein R 1 is the radical of the formula VI ##STR5## wherein each of R 9 , R 10 and R 11 independently of one another is hydrogen, halogen, carbamoyl, cyano, trifluoromethyl, C 2 -C 13 alkylcarbamoyl, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 1 -C 12 alkylmercapto, C 2 -C 13 alkoxycarbonyl, C 2 -C 13 alkanoylamino or phenoxy, phenylmercapto, phenoxycarbonyl, phenylcarbamoyl or benzoylamino, each unsubstituted or substituted by halogen, C 1 -C 12 alkyl or C 1 -C 12 alkoxy, with the proviso that at least one of R 9 , R 10 and R 11 is hydrogen.
  • preferred starting materials are compounds of the formula II, wherein R 1 is the radical of the formula VII ##STR6## wherein one of R 12 and R 13 is chlorine, bromine, C 1 -C 4 alkyl, cyano, C 1 -C 4 alkoxy, or is phenoxy, carbamoyl or C 2 -C 5 alkylcarbamoyl, each unsubstituted or substituted by chlorine or methyl, or is phenylcarbamoyl which is unsubstituted or substituted by chlorine, methyl or methoxy, and the other is hydrogen.
  • X is bromine or chlorine
  • M is sodium, potassium, magnesium or zinc
  • m is 0 or 1
  • Z is C 1 -C 8 alkyl.
  • X is bromine
  • M is zinc
  • m is 1
  • Z is C 1 -C 5 alkyl.
  • Y is bromine or chlorine and Z is C 1 -C 8 alkyl, preferably C 1 -C 5 alkyl. It is most preferred to use methyl bromoacetate or ethyl bromoacetate.
  • Nitriles preferably used as compounds of the formula IV and V in the process of this invention are those in which R 1 and R 2 are unsubstituted phenyl or naphthyl or phenyl or naphthyl which carry non-water-solubilising substituents. It is most preferred to use nitriles of the formulae IV and V in which R 1 and R 2 are radicals of the formula VI, preferably of formula VII.
  • the reaction of the compounds of formulae II and III with the compound of formulae IV and V is carried out in an organic solvent.
  • suitable solvents are ethers such as tetrahydrofuran, dioxan, anisole or diphenyl ethers, or glycol ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether or diethylene glycol diethyl ether; as well as dipolar aprotic solvents such as dimethylformamide, N,N-dimethylacetamide, nitrobenzene, N-methylpyrrolidone; aliphatic or aromatic hydrocarbons or mixtures thereof such as benzene or benzene substituted by alkyl or halogen, e.g.
  • toluene, xylene, trimethylbenzene, isopropylbenzene or chlorobenzenes it is also possible to use the nitrile of the formula IV or V as solvent if it is liquid in the temperature range in which the reaction takes place. Mixtures of the above solvents may also be used. It is convenient to use 5 to 20 parts by weight of solvent per 1 part by weight of the total amount of the reactants.
  • an ether or an aromatic hydrocarbon as solvent, in particular ethylene glycol dimethyl ether, tetrahydrofuran, dioxan, anisole, toluene, o-, m- or p-xylene, trimethylbenzene or isopropylbenzene.
  • the process of the invention is preferably carried out in the temperature range from 60° to 160° C., preferably from 90° to 140° C.
  • the compound of formula I can be isolated by filtration. This is conveniently done by diluting the reaction solution, before filtration, with an organic solvent, e.g. acetone, and washing the compound of formula I with water after filtration. In addition to the water used for washing it is possible to employ an inorganic or organic acid, e.g. hydrochloric acid or acetic acid.
  • an organic solvent e.g. acetone
  • an inorganic or organic acid e.g. hydrochloric acid or acetic acid.
  • reaction vessel In the process for the preparation of the compounds of formula I, it is in principle possible to charge the reaction vessel, at low temperature, with all the components and then to heat the mixture to the range of the reaction temperature, or to add the individual components, in any order, to each other in the range of the reaction temperature.
  • a preferred embodiment of the reaction which usually has a particularly advantageous influence on the yield, consists in charging the reaction vessel with the compound of formula II together with the aromatic nitrile of the formula IV or V and then adding the compound of formula III in the range of the reaction temperature. It is entirely possible to carry out the process of the invention not only batchwise, but also continuously. Although it usually suffices to employ stoichiometric amounts of the reactants, the yield can be improved by using in particular an excess of up to about 2.5 moles of the compound of formula IV or V per mole of compound of the formula II.
  • the compounds of formula II can be obtained by reacting a compound of the formula VIII ##STR7## wherein R 1 and Z are as defined above, with a metal M or metal salt MX m , wherein M, X and m are as defined above, under conditions which are known per se.
  • the compounds of formula VIII can in turn be prepared by different known methods, for example by reacting cyanoacetates with organometal compounds of the R 1 MgX type, wherein X is halogen.
  • the compounds of formula I may also be used as polymer-soluble colourants. Normally, however, the compounds of formula I are used as pigments for organic materials of high molecular weight and can be used in general direct in the form in which they are obtained by the process of this invention.
  • the pigments obtained by the process of the invention can be converted into a more opaque or more transparent form.
  • xylenes chlorobenzene, o-dichlorobenzene or nitrobenzene, as well as pyridine bases such as pyridine, picoline or quinoline, and also ketones such as cyclohexanone, ethers such as ethylene glycol monomethyl or monoethyl ether, amides such as dimethylformamide or N-methylpyrrolidone, and also dimethylsulfoxide or sulfolane.
  • the aftertreatment may also be carried out in water in the presence of an organic solvent and/or with the addition of surface-active compounds.
  • Organic materials of high molecular weight which may be pigmented with the compounds of formula I are e.g. cellulose ethers and esters such as ethyl cellulose, nitrocellulose, cellulose acetate, cellulose butylate, natural resins or synthetic resins such as polymerisation resins or condensation resins, e.g.
  • aminoplasts in particular urea/formaldehyde and melamine/formaldehyde resins, alkyd resins, phenolic plastics, polycarbonates, polyolefins such as polystyrene, polyvinyl chloride, polyethylene, polypropylene, polyacrylonitrile, polyacrylates, polyamides, polyurethanes or polyesters, rubber, casein, silicone and silicone resins, individually or in mixtures.
  • the above organic compounds of high molecular weight are in the form of plastics, melts or of spinning solutions, lacquers, paints or printing inks.
  • the pigments of this invention in the form of toners or formulations.
  • the compounds of the formula I are employed in an amount of preferably 0.1 to 10% by weight, based on the organic material of high molecular weight to be pigmented.
  • the colorations obtained e.g. in plastics, filaments, lacquers or printing inks, have excellent tinctorial strength, good dispersibility, good fastness to overspraying, migration, heat, light and atmospheric influences, as well as good gloss.
  • the salt of formula IX is dissolved in 50 ml of benzonitrile and to this solution are added 8.35 g (0.05 mole) of ethyl bromoacetate. The mixture is stirred for 8 hours at 120° C., then the red suspension is cooled, diluted with 50 ml of acetone, and stirred for another 10 minutes. The batch is filtered and the residue is washed with acetone and purified by boiling it in 25 ml of glacial acetic acid for 4 hours at reflux temperature. The product is isolated by filtration, washed once more with acetone and dried at 80° C. in vacuo, affording 3.2 g (22% of theory, based on ethyl bromoacetate) of pure pigment of the formula X ##STR9## which colours PVC red.
  • the salt of formula XI is suspended in 30 ml of xylene and to the suspension are added 8.35 g (0.05 mole) of methyl bromoacetate and 15.5 g (0.113 mole) of p-chlorobenzonitrile. The mixture is stirred for 8 hours at 120° C.
  • Working up as in Example 1 yields 4.2 g (26% of theory, based on methyl bromoacetate) of the pigment of formula XII ##STR11## which colours PVC red.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
US06/512,074 1982-07-08 1983-07-08 Preparation of 1,4-diketopyrrolo-[3,4-c]pyrroles Expired - Lifetime US4613669A (en)

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JP (1) JPS5924758A (enrdf_load_stackoverflow)
DE (1) DE3367931D1 (enrdf_load_stackoverflow)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4681971A (en) * 1984-11-07 1987-07-21 Ciba-Geigy Corporation Phenyl substituted aminodicarboxylate esters
US4778899A (en) * 1984-11-07 1988-10-18 Ciba-Geigy Corporation Process for the preparation of pyrrolo (3,4-c) pyrroles
US4791204A (en) * 1985-11-26 1988-12-13 Ciba-Geigy Corporation 1,4-diketopyrrolo[3,4-c]pyrrole pigments
US4810304A (en) * 1987-02-02 1989-03-07 Ciba-Geigy Corporation Solid solutions of pyrrolo-(3,4-C)-pyrroles with quinacridones
US4931566A (en) * 1987-07-31 1990-06-05 Ciba-Geigy Corporation Process for the preparation of pyrrolo[3,4-c]pyrroles
WO2002068422A3 (en) * 2001-01-05 2003-01-30 Sun Chemical Corp Syntheses for preparing 1,4-diketopyrrolo[3,4-c]pyrroles
US20040250732A1 (en) * 1999-07-09 2004-12-16 Yves Grandidier Pigments having improved colouristic properties and process for their preparation
US20050234243A1 (en) * 2002-07-10 2005-10-20 Grimm Felix W Novel diketopyrrolopyrrole pigments

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0061426B1 (de) * 1981-03-20 1985-02-13 Ciba-Geigy Ag Verfahren zum Färben von hochmolekularem organischem Material und neue polycyclische Pigmente
US4585878A (en) * 1983-06-29 1986-04-29 Ciba-Geigy Corporation N-substituted 1,4-diketopyrrolo-[3,4-c]-pyrroles
EP0181290B1 (de) * 1984-11-07 1991-09-18 Ciba-Geigy Ag Pigmentmischungen
EP0748851B1 (de) * 1995-06-15 2001-05-09 Ciba SC Holding AG Pigmentzusammensetzungen aus Diketopyrrolopyrrolen
JP2006342167A (ja) * 2000-01-06 2006-12-21 Toray Ind Inc ジケトピロロ［３，４−ｃ］ピロール誘導体
WO2009144115A1 (en) 2008-05-28 2009-12-03 Basf Se Improved, red colour filter composition
KR102806570B1 (ko) 2018-06-25 2025-05-14 썬 케미칼 비.브이. 컬러 필터용 적색 안료 조성물

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0061426A1 (de) * 1981-03-20 1982-09-29 Ciba-Geigy Ag Verfahren zum Färben von hochmolekularem organischem Material und neue polycyclische Pigmente

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0061426A1 (de) * 1981-03-20 1982-09-29 Ciba-Geigy Ag Verfahren zum Färben von hochmolekularem organischem Material und neue polycyclische Pigmente

Non-Patent Citations (11)

* Cited by examiner, † Cited by third party
Title
Arsenijevic et al., Bulletin de la Societe Chimique de France 3403 3408, (1968). *
Arsenijevic et al., Bulletin de la Societe Chimique de France 3403-3408, (1968).
Dardoize et al., Bulletin de la Societe Chimique de France 3841 3846, (1972). *
Dardoize et al., Bulletin de la Societe Chimique de France 3841-3846, (1972).
Farnum et al., Tetrahedron Letters 29, 2549 2552, (1974). *
Farnum et al., Tetrahedron Letters 29, 2549-2552, (1974).
Iimori et al., Tetrahedron Letters, 27, 2525 2528 (1979). *
Iimori et al., Tetrahedron Letters, 27, 2525-2528 (1979).
Kagan et al., Bulletin de la Societe Chimique de France 1819 1822, (1966). *
Kagan et al., Bulletin de la Societe Chimique de France 1819-1822, (1966).
Santaniello et al., Synthesis 698 (Oct. 1977). *

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4681971A (en) * 1984-11-07 1987-07-21 Ciba-Geigy Corporation Phenyl substituted aminodicarboxylate esters
US4778899A (en) * 1984-11-07 1988-10-18 Ciba-Geigy Corporation Process for the preparation of pyrrolo (3,4-c) pyrroles
US4791204A (en) * 1985-11-26 1988-12-13 Ciba-Geigy Corporation 1,4-diketopyrrolo[3,4-c]pyrrole pigments
US4914211A (en) * 1985-11-26 1990-04-03 Ciba-Geigy Corporation Pigment compositions
US4810304A (en) * 1987-02-02 1989-03-07 Ciba-Geigy Corporation Solid solutions of pyrrolo-(3,4-C)-pyrroles with quinacridones
US4931566A (en) * 1987-07-31 1990-06-05 Ciba-Geigy Corporation Process for the preparation of pyrrolo[3,4-c]pyrroles
US20040261662A1 (en) * 1999-07-09 2004-12-30 Yves Grandidier Pigments having improved colouristic properties and process for their preparation
US20040250732A1 (en) * 1999-07-09 2004-12-16 Yves Grandidier Pigments having improved colouristic properties and process for their preparation
US20040250733A1 (en) * 1999-07-09 2004-12-16 Yves Grandidier Pigments having improved colouristic properties and process for their preparation
US6911074B2 (en) * 1999-07-09 2005-06-28 Ciba Specialty Chemicals Corp. Pigments having improved coloristic properties and process for their preparation
US6913642B2 (en) * 1999-07-09 2005-07-05 Ciba Specialty Chemicals Corp. Pigments having improved coloristic properties and process for their preparation
WO2002068422A3 (en) * 2001-01-05 2003-01-30 Sun Chemical Corp Syntheses for preparing 1,4-diketopyrrolo[3,4-c]pyrroles
US20050234243A1 (en) * 2002-07-10 2005-10-20 Grimm Felix W Novel diketopyrrolopyrrole pigments
US7002021B2 (en) 2002-07-10 2006-02-21 Clariant Gmbh Diketopyrrolopyrrole pigments

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EP0098808A2 (de) 1984-01-18
DE3367931D1 (en) 1987-01-15
JPH0414144B2 (enrdf_load_stackoverflow) 1992-03-11
EP0098808B1 (de) 1986-11-26
JPS5924758A (ja) 1984-02-08
EP0098808A3 (en) 1984-11-28

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